N-hydroxyethylated derivatives of 1-amino- or 2-amino-5-hydroxynaph thalene-7-sulphonic acid



Patente were? d Aug. 23, 1932 enone MATZDORF, or nnssAu manna N-HYDROXYETEYLATE No Drawing. Application filed January 3, 19

thalene dc N-hydroxyethyl 2 amino-5-hydroxynap 5 acid and same.

I have 5-hy droxy smoothly acids.

2 amino-5 acid and products.

1 amino acid and to perform and I prefer with an inlet avoid a loss of the latter. My new formed at the be for instance,

C. and finished at room temperameans to at 30 to ocess preferably is per WORKS, INC., OF NEW YORK,

resent invention relates to new naphtives and more particularly to derivatives of l-aminoor hthalene-7 -sulphonic f manufacturing the riva to a process 0 found th naphthalene-'T-sulphonic .hy without formation 0 5-hydroxyn of Q-aminod are valuable interme manufacture of dyes.

aphthalene in a closed vessel. the reaction betw proceeds so smooth the reac for the ethylene oxide and ginning at a raised temperature,

ture within 12 to 24 hours while stirring The quantity of 0 erally surpasses th mono-sub main the excess of ethylene oxide, 1 use,

I prefer to use about the mono-substituted derivative.

ethylene at 'l-aminoand Q-aminoacid are transformed into the correspond- 0 ing N-hydr-oxyeth with ethylene oxide upon of the alkali metal salts o In contra hydroxynaphthalene sulphonic acids,

5 action proceeds smoothly wi yl derivatives by acting an aqueous solution f the said sulphonic distinction to other aminothe reth the l-amino or droxynaphthalene 7 sulphonic f worthless by-' N-hydroxyethyl derivatives of -7 -sulpl1onic 5-hydroxynaphthalenealkali metal salt 7 hydroxynaphthaethylene oxide may However, cen the said components lythat it is not necessary tion in a pressure vessel to use a reaction vessel provided at required to form the N- stituted aminohydroxynaphthalene compound and ble quantity. Nevertheless, I obtain in the oxide is easily removedv ALT, GERMANY, ASSI GNOB TO GENERAL A'NILINE N. Y., A CORPORATION 6F. DELAWARE I DERIVATZVES OF LAMINO 0B Z-AMINO-E-HYDBOXYNAPH- THALENE-Y-SULPHONIC ACID 30, Serial No. 418,417, and in Germany January 7, 1929.

from the solution containing the reaction mass by boiling. V The following examples serve to illustrate my invention, the. parts being by weight 2-1 Emample 1.239 parts of 2-amino-5-l ydroxynaphthalene-T-sulphonic acid are .dissolved in form of the sodium salt in about 2000 parts ofwater and at a teniperatureof 30 to 50 CL, while stirring, to parts I g of gaseous ethylene oxide are introducedv into the solution, Then the reacting liquid is stirred for 12 to 24 hours, care being taken that the ethyleneoxi'de introduced into the solution does not escape from the reaction vessel, The reaction is finished, if a sample acidified: with mineral acid, does not form a diazo compound after addition .of sodium nitrite. I I

The solution of the N-hydroxyethylated W aminohydroxynaphthalene sulphonic' acid 5;, may be used directly in the manufacture of dyes. By evaporating the solution the sodiuni salt of N-hydroxyethylated 2-amino-5 hydroxynaphthalene-'Y-sulphonic' acid is obtained forminga resinous mass or when pulverized, a lightgray powders The new acid easily dissolves in water; from the aqueous solution it is separated neither by amineral acid. nor by addition of common salt. Ewamplc 2.

diate -289 parts of l-arn1no 5-hydroxynaphthalene;7-sulphonic acid in form of the sodium salt, are dissolved inQOO O parts of water and treated with ethylene oxide under the conditions given'in'example 1. The, solution of N-hydroxyethylated 1-amino-5- hydroxynaphthalene-Wsulphonic acid may be used directly in the manufacture of dyes. hen adding 100 parts of hydrochloric acid of 23 B. to the solution while stirring, the new acid is obtained after cooling in crystallized form. The crystals are filtered with suciti.on,.was hed with a small quantity ofcol'd water and dried, whereat .the 1- (N-hydroxyethyl) -amino 5: hydroxynaphthalenefl S111, the form of a nearly 9 i with gendou- The

phonic acid is obtained in colorless crystalline powder. The acid'is wherein one X means NH represents H.

. 2. The process rwh'ich' comprises about 80 parts of ethylene oxide to an aqueous solution of about 239 parts of l-amin'o-"5-hydroxynaphthalene-7-sulphonic acid in the form of the sodium salt. while-stirring, at a temperature of about 30 to about 50 (3., and stirring the reaction solution at room temperature for aboutlQ to about 24 hours.

nd othe 6. As a new product the 2- (beta hydroxy' ethyl) -amino-5-hydroxynaphthalene 7 sulphonicacid of the formula forming in the form of its sodium salt a grayish-white powder easily soluble in water and not precipitated byaddition of hydrochloric acid or common salt. a In testimony whereof, I affix my signature.

.GEOBG MAT ZDORF.

adding a 3. The process which comprises adding about '80 parts of ethylene oxide to an aqueous solution of about 239 parts of 2-amino-'5- V hydroxynaphthalene fisulphonic acid in form of the sodium salt while stirring at a temperature of about .30 to about 50 (Land stirring the reacting solution at room 'ature for about 12 to about 24 hours.

4. As new products the N-hydroxyethylattempered amino-naphthalene sulphonic acids of the a general formula wherein one Xjmeans the .radicle V .NHCH CH OH antithe other X means H these compounds bein g soluble in 7 sodium salts and yielding valuable dyes when coupled with aromatic diazo compounds. 5. As a new ethyl).-an1ino 5-hydroxynaphthalene-7 suflithe free 'acid being water, but easily soluble in hot water, re} -crystallizing from hot water, in large 'ccoloriless phonic acid of'the formula:

' NOH2CH2OH slightly soluble in. mid

crystals.

water in the form of their product the 1-'( beta hydroxy 

